Isopropanol → 2-Chloro-7-phenylthieno[3,2-d]pyrimidine

HRID 1803911Notes

Reaction equation

HRID 1803911 reaction equation
Br[C:2]1[C:6]2[N:7]=[C:8]([Cl:11])[N:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:11][C:8]1[N:9]=[CH:10][C:5]2[S:4][CH:3]=[C:2]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 569657247-Bromo-2-chlorothieno(3,2-d)pyrimidine

Product 1

HCID 582288992-Chloro-7-phenylthieno[3,2-d]pyrimidineYield 141.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-bromo-2-chlorothieno[3,2-d]pyrimidine (1.0 g, 4.0 mmol), phenyl boronic acid (0.6 g, 4.9 mmol), Pd[PPh3]4 (0.47 g, 0.4 mmol) and aqueous sodium carbonate (2M, 4.5 mL, 9.0 mmol) in toluene (25 mL)/isopropanol (8 mL) was heated under reflux overnight. The mixture was allowed to cool to room temperature, was diluted with ethyl acetate then washed with 10% aqueous sodium bicarbonate, dried (Na2SO4) filtered and concentrated. The resultant solid was sonicated in diethyl ether (2×70 mL) and the combined ether washes were evaporated to afford the crude product (1.4 g), still containing starting material and OPPh3.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. washthen washed with 10% aqueous sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant solid was sonicated in diethyl ether (2×70 mL)
  8. customthe combined ether washes were evaporated

Sources & evidence

ORD record
ord-2a30c81c01914e5a8e36d25433f76036
Source dataset
uspto-grants-2013_01
Patent number
US08354408B2

Reaction notes

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